If You Are Going to Wear Heels This Winter, This Is How to Do It

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@chrissyford

On Chrissy Rutherford: BY FAR bag

Leather pants and black boots are always a winning combo. 

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@missenocha

On Enocha Tellus: Zara boots

It doesn't get chicer than a textured sweaterdress and knee-high heeled boots. 

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@alyssainthecity

On Alyssa Coscarelli: Staud Large Moon Bag 

Little block-heel boots make tailored trousers look even more polished.

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@lefevrediary

On Amy Lefévre: Schutz boots

The only thing that can make a jumpsuit cooler is a pair of heeled boots. 

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@champagnemani

On Imani Randolph: For Love & Lemons dress

Hello, date-night look!

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@aimeesong

On Aimee Song: Chloé bag

When in doubt, go monochrome. 

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@bettinalooney

On Bettina Looney: Bottega Veneta The Pouch Large Clutch ($2700)

Make your favorite heels work for winter by adding opaque tights. 

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@slipintostyle

On Ellie: Stand Studio coat; Saks Potts pants; Charles & Keith shoes, Le Specs The Last Lolita Sunglasses ($119)

Mixing prints and bold colors gets taken up a notch with the addition of heeled ankle boots.

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@deborabrosa

On Débora Rosa: Mango outfit

Make a Canadian tuxedo even cooler with black heeled ankle boots (and maybe throw on a big coat top when heading out). 

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@anoukyve

On Anouk Yve: Jimmy Choo boots; Little Liffner bag

Dress up your favorite coat and thick scarf with a pair of knee-high heeled boots. 

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@ada_oguntodu

A cool outfit gets even cooler with sleek heeled ankle boots. 

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@emilisindlev

The best way to add a pop of color to an otherwise neutral outfit? Bright-hued heels. 

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@natashandlovu

On Natasha Ndlovu: Alexander McQueen coat; Bottega Veneta Jodie Mini Bag ($1720)

Your favorite sweaterdress was made to be paired with pumps. 

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@dolcecurvy

The classic combination of a turtleneck sweater, trousers, and a black coat suddenly feels modern when styled with heeled black ankle boots. 

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@venswifestyle

On Renia Jaz: Bottega Veneta The Chain Pouch ($3600)

Camel always looks expensive—even more so when paired with neutral-colored pumps. 

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@symphonyofsilk

On Lorna: Polène bag

Give your favorite blazer-and-skinny-jeans outfit a fun twist with heeled boots (bonus points if they're snake print). 

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@smythsisters

On Marianne Smyth: Levi's jeans

The perfect dinner-at-home look includes a white button-down, black jeans, heeled boots, and a chunky scarf. 

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@babba

Colored coats are always fun, and heeled black ankle boots just make them feel a touch more polished. 

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@amandasorensonn

White heeled boots were made to be worn with plaid coats. 

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@femmeblk

On Lydia Tsegay: Polène bag; Zara T-shirt; Sentaler coat

Strappy heels with an all-white look are as aspirational as it gets. 

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@polliani

On Janka Polliani: Gucci bag and Off-White Tights ($120)

This feels like a modern-day Blair Waldorf outfit—in a good way. 

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@ileniatoma_

On Ilenia Toma: Gucci GG Marmont Mini Bag ($950)

Note to self: Invest in tights. 

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@greceghanem

On Grece Ghanem: Zara blazer

A simple blazer and jeans are suddenly an outfit with the addition of unique heels. 

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@styleheroine

On Evangelie Smyrniotaki: Woolrich jacket

Slightly baggy jeans feel balanced with a lift from sleek pumps.